title: Unprecedented noncatalyzed anti-carbozincation of diethyl acetylenedicarboxylate through alkylzinc group radical transfer.
abstract: The radical carbozincation of diethyl acetylenedicarboxylate, performed at room temperature in the presence of air, leads to fumaric derivatives through a selective alkylzinc group radical transfer controlled by coordination. The total trans stereocontrol is unprecedented, carbocupration is well-known to give the reversal selectivity at low temperature, while classical radical addition methodologies lead to mixtures of isomers.
authors.affiliation: Laboratoire Chimie Provence, UMR 6264, Equipe CMO, case 562, Université Aix-Marseille, FST Saint-Jérôme, av. Escadrille Normandie Niemen, 13397 Marseille cedex 20, France.
authors.forename: Julien
authors.initials: J
authors.lastname: Maury
authors.forename: Laurence
authors.initials: L
authors.lastname: Feray
authors.forename: Michèle P
authors.initials: MP
authors.lastname: Bertrand